US5559102AExpiredUtility

Adenosine and guanosine-3'-5'-cyclic methylphosphonate derivatives

39
Assignee: NIPPON SHINYAKU CO LTDPriority: Aug 16, 1988Filed: Jan 13, 1994Granted: Sep 24, 1996
Est. expiryAug 16, 2008(expired)· nominal 20-yr term from priority
C07H 19/20
39
PatentIndex Score
3
Cited by
17
References
26
Claims

Abstract

Cyclic AMP and cyclic GMP derivatives, such as 8-bromoadenosine-3', 5'-cyclic methylphosphonate, are effective in inhibiting phosphodiesterases.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound of the formula ##STR7## wherein R 1  is hydrogen, hydroxyl or acyloxy; R 2  is lower alkyl; R 3  is hydrogen, methyl or acyl; and R 4  is hydrogen or halo; provided that when R 1  is hydrogen and R 2  is lower alkyl, R 3  and R 4  are not both hydrogen. 
     
     
       2. A compound according to claim 1 wherein R 3  is hydrogen, methyl or acyl of the formula --COR 31  wherein R 31  is lower alkyl or aryl. 
     
     
       3. A compound according to claim 2 wherein R 31  is alkyl of 1 to 4 carbon atoms. 
     
     
       4. A compound according to claim 2 wherein R 31  is phenyl or naphthyl. 
     
     
       5. A compound according to claim 1 wherein R 4  is hydrogen, bromo, chloro or fluoro. 
     
     
       6. A compound according to claim 1 wherein R 6  is hydrogen, bromo, chloro or fluoro. 
     
     
       7. A compound according to claim 1 wherein R 2  is alkyl of 1 to 4 carbon atoms. 
     
     
       8. A pharmaceutical composition which comprises a compound of the formula ##STR8## wherein R 1  is hydrogen, hydroxyl or acyloxy; R 2  is lower alkyl; R 3  is hydrogen, methyl or acyl; and R 4  is hydrogen or halo; provided that when R 1  is hydrogen and R 2  is lower alkyl, R 3  and R 4  are not both hydrogen in combination with a pharmaceutically acceptable carrier. 
     
     
       9. A composition according to claim 8 wherein R 31  is hydrogen, methyl or acyl of the formula --COR 31  wherein R 31  is lower alkyl or aryl. 
     
     
       10. A composition according to claim 9 wherein R 31  is alkyl of 1 to 4 carbon atoms. 
     
     
       11. A composition according to claim 9 wherein R 31  is phenyl or naphthyl. 
     
     
       12. A composition according to claim 8 wherein R 4  is hydrogen, bromo, chloro or fluoro. 
     
     
       13. A pharmaceutical composition which comprises a compound of the formula ##STR9## wherein R 1  is hydrogen, hydroxyl or acyloxy; R 2  is lower alkyl; R5 is hydrogen or acyl and R 6  is hydrogen or halo in combination with a pharmaceutically acceptable carrier. 
     
     
       14. A composition according to claim 13 wherein R 5  is hydrogen or acyl of the formula --COR 51  wherein R 51  is lower alkyl or aryl. 
     
     
       15. A composition according to claim 14 wherein R 51  is alkyl of 1 to 4 carbon atoms. 
     
     
       16. A composition according to claim 14 wherein R 51  is phenyl or naphthyl. 
     
     
       17. A composition according to claim 13 wherein R 6  is hydrogen, bromo, chloro or fluoro. 
     
     
       18. A composition according to claim 8 wherein R 2  is alkyl of 1 to 4 carbon atoms. 
     
     
       19. A compound of the formula ##STR10## wherein R 1  is hydrogen, hydroxyl or acyloxy; R 2  is lower alkyl; R 5  is hydrogen or acyl and R 6  is hydrogen or halo. 
     
     
       20. A compound according to claim 19 wherein R 1  is hydroxyl or acyloxy. 
     
     
       21. A compound according to claim 19 wherein R 2  is alkyl of 1 to 4 carbon atoms. 
     
     
       22. A composition according to claim 13 wherein R 1  is hydroxyl or acyloxy. 
     
     
       23. A composition according to claim 13 wherein R 2  is alkyl of 1 to 4 carbon atoms. 
     
     
       24. A compound according to claim 19 wherein R 5  is hydrogen or acyl of the formula --COR 51  wherein R 51  is lower alkyl or aryl. 
     
     
       25. A compound according to claim 24 wherein R 51  is alkyl of 1 to 4 carbon atoms. 
     
     
       26. A compound according to claim 24 wherein R 51  is phenyl or naphthyl.

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